


Ride 'Em Cowboy

by nickelkeep



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Chaps, Cowboy Hats, Established Castiel/Dean Winchester, M/M, Panties, Plot What Plot/Porn Without Plot, Rutting, SPN Song Challenge Bingo, Sexual Roleplay, Song: Pony
Language: English
Status: Completed
Published: 2019-05-02
Updated: 2019-05-02
Packaged: 2020-02-15 19:49:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,391
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18676294
Author URL: https://archiveofourown.org/users/nickelkeep/pseuds/nickelkeep
Summary: There are two things everyone should know about Dean Winchester. He loves Cowboys, and he always cheats at poker. Cas forgot the second one.





	Ride 'Em Cowboy

**Author's Note:**

  * For [quinnvicious](https://archiveofourown.org/users/quinnvicious/gifts).



> Also written for the [SPN Song Challenge Bingo](https://spnsongchallengebingo.tumblr.com/), Free Space, Song Chosen:[Far - Pony](https://open.spotify.com/track/2tqfby2Fedl25lsJN7mRjV?si=QPk7yl8CTyKtc5KcX5oqXA) (Yes I know it's not the original, so sue me.)
> 
> \--Updated to add the beautiful work from Fleet, which can be found at [his twitter.](https://twitter.com/demonfleet/status/1124797518641074176)
> 
> As always, constructive critiques are welcome and helpful.
> 
> You can find me on [Tumblr](https://nickelkeep.tumblr.com/) and [Pillowfort](https://www.pillowfort.io/nickelkeep)

“Dean, I know I said I would do anything you asked but are these really necessary?” Cas called out from behind the changing screen in their room.

“Yes.” Dean thanked his lucky stars that Cas hadn’t figured out that he had cheated at poker that night as he repeated himself under his breath. “Hell, yes.” He sat on their bed and stared at Cas’ silhouette moving gracefully.

Cas stepped out from behind the screen. Dean’s heart stopped, and his jaw hit his chest. From the number of times he had shared the bed with his angel, he knew that Cas was muscular, well-built, and well-hung. What he didn’t expect was how hard the cowboy hat and chaps would make him. He licked his lips as he devoured Cas with his eyes.

A smirk played over Cas’ lips once he noticed what his appearance was doing to Dean. “Howdy, Cowboy.”

Dean whimpered in response, a small noise escaping the back of his throat. All of the blood rushing to his cock had left him at a loss for coherent thought.

Cas walked over to Dean and posed, putting his foot up on the bed. “I feel like one of us overdressed for this rodeo, don’t you Dean?”

Dean swallowed hard and nodded, as he reached for the hem of his shirt. As he lifted his shirt over his head, he felt Cas’ hands start to wander over his chest. “Such a pretty little thing.” Dean felt the blush creep up his cheeks and ears as he threw his shirt to the side. Cas pushed him so his back was flat on the bed. “I wonder if you’ve been broken in.” Cas’ hands traced down Dean’s chest and stopped on his belt. The angel slowly pulled at the leather, undoing the binding as well as Dean’s resolve.

Another whimper escaped Dean’s lips as Cas unbuttoned and unzipped his jeans. Even with the tight, constricting fabric removed, his cock still strained, held down by his satin panties. “Cas, please?”

Dark, beautiful, lust settled into the blue eyes appraising Dean. Cas palmed his hunter’s cock through the fabric before straddling him. “Please what?”

Dean’s eyes closed and his hips arched up to rut against Cas. “I need you. This is…” Dean stuttered as words escaped him, and chose to point instead. “This is so much.”

Cas’ laugh was deep and warm as he slid his chest up against Dean’s. “This is what you said you wanted.” Cas nipped at Dean’s neck before playfully sucking on his earlobe. “The things I can do to you and your body Dean.”

“Cas, fuck.” Dean’s hands instantly slid up Cas’s arm and down his back. “I’m going to come in my underwear if you keep this up.”

“Well, then partner.” Cas pushed himself back up and fixed his hat, “Can’t have that without breaking you in first.”

Dean breathlessly chuckled at Cas’ attempt to stay in character, before whining at the cold that was biting at his skin. Cas stood up and removed Dean’s pants. “As much as I love these,” Cas rubbed Dean’s cock through the satin panties with his own, “they are definitely in the way.” Dean whimpered and nodded as he lifted his hips again, giving Cas the access to pull off the flash of pink that had restrained him.

Cas bit his bottom lip as he straddled his hunter again. “I guess these… chaps, you called them? Do have a significant advantage.” He leaned over to the nightstand and grabbed the lube that was already pulled out in preparation. Dean watched with half-lidded eyes as Cas squirted some of the lube onto his hand and stroked his cock. The movement was mesmerizing, and Dean gasped in surprise when his angel pressed their cocks together. Between Cas’ warm, slick hands holding them together, their thrusting and jerking, and the friction of their cocks rubbing up against each other, Dean whimpered in warning, “Cas, I’m going to come.”

Cas pulled away and squeezed the base of Dean’s cock. “Slow your roll, Cowboy. It ain’t time for that yet.” He kept slowly stroking his own cock as he admired his lover under him. “I want you to come on my cock.”

A combination of a whimper and a chuckle escaped Dean’s throat. “Can I save a horse and ride a cowboy?”

“Can you handle the ride?” Cas growled before standing up and flipping Dean over, pulling his ass into the air. A low, heady moan fell from Dean’s lips as his cowboy’s tongue lapped over his tight hole. Exquisite curses flowed from his mouth while he gripped the sheets of their bed.

Cas stopped, barely long enough to give Dean a chance to catch his breath, as he lubed his fingers back up and slowly slid one inside. “Still want a ride, Dean?”

Dean’s back arched downward, like a cat stretching, as he whimpered and squirmed under Cas’ touch. “More, please. More.” A second finger joined the first, and together they thrust in and out, scissoring as Cas expertly stretched and prepared Dean.

“I don’t think you can ride yet. The saddle isn’t quite warm enough yet.” Cas pressed against Dean, letting him feel the combination of leather and skin. Cas added a third finger to the others and purposely brushed his middle finger up against Dean’s prostate.

Dean cried out in pleasure, pleading with his angel, “Cas, I’m not going to last for the ride if you keep this up.” He felt Cas’ hand wrap around the base of his cock again and squeeze hard. He whimpered at being edged but knew that coming on Cas’ cock would be worth it in the end.

As if on cue, Cas’ fingers slid out of Dean’s ass, and he back laid on the bed. A curled finger beckoned Dean over, who in response crawled across the bed. The hunter licked his lover’s cock from base to tip before taking it in his mouth. Dean looked up at Cas, teasing with the quick suck and blow, before moving up his body further and straddling him.

Dean grabbed the bottle of lube this time, and after getting some in his own hand, reached behind him and started stroking Cas’ cock. “Just warming up the saddle, partner,” Dean quipped. Dean lined Cas’ cock with his lubed and stretched hole and pressed himself down onto it. He closed his eyes at the pleasure and pressure, his breath catching as he took more of Cas’ length inside.

Once bottomed out, he let out his breath and looked at his angel beneath him. Cas was biting his bottom lip, staring darkly at Dean.

Cas smirked and drove his hips up, ripping a throaty moan out of Dean. “I thought you wanted to ride?” Cas ran his hands up Dean’s thighs and grabbed his hips. “Show me your skills, cowboy.”

Dean began to move on his own, sliding up and down, grinding. Cas’ hips thrust up to meet each of Dean’s movements. Dean moaned and mewled at each thrust, his angel closer to pushing him over the edge.

“Come for me. Don’t touch yourself. I know you don’t need to.” Cas’ breaths were shorter and faster, his own release not too far away.

Dean held onto Cas’ arms, steadying himself as he moved faster, burying Cas’ cock as deep as it could go. He found the right angle to make sure his spot was getting hit with each movement, and just a few thrusts later, he found himself coming. Hot, thick spurts of come shot up both his and Cas’ stomachs and chests. He moaned in ecstasy, his hands sliding to meet Cas’ on his hips as he continued to ride his cowboy.

Cas cried out shortly after, his orgasm washing over him and his come filling Dean. He released his grip on Dean’s hips and let out a tired chuckle. “Sorry if that leaves bruises.”

“You’ve left worse.” Dean leaned forward and kissed Cas before sliding off and to the side to curl against his lover. “Damn, that was hot.”

“Temperature-wise, or sensually?” Cas asked as he took off the cowboy hat and set it on Dean’s head. “I believe you deserve to wear this. You were the one ‘riding the pony.’”

Dean laughed and nuzzled into Cas’ chest. “Bull, Angel. I rode the bull.”

**Author's Note:**

> Are you into Dean and Cas? Do you use Discord? Looking for a cool group of people to hang out with? Come join the writers, artists, and Destiel fans on the [Profound Bound Discord Server](http://discord.profoundbond.net/).


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